钌催化的烯基环丙烷重排反应。不同的反应途径。
Ruthenium Catalyzed Rearrangement of Ene-cyclopropenes. Divergent Reaction Pathways.
作者信息
López-Rodríguez Alberto, Domínguez Gema, Pérez-Castells Javier
机构信息
Facultad de Farmacia, Dpto. Química y Bioquímica , Universidad San Pablo CEU , Urb. Montepríncipe, Boadilla del Monte , 28668 Madrid , Spain.
出版信息
J Org Chem. 2019 Jan 18;84(2):924-933. doi: 10.1021/acs.joc.8b02849. Epub 2019 Jan 9.
The reaction of ene-cyclopropenes with Cp*RuCl(cod) leads to alkenyl bicyclo[3.1.0]hexanes, bicyclo[4.1.0]heptanes, and bicyclo[5.1.0]octanes. This reaction involves a reverse regioselectivity in the cyclopropene opening than with gold chlorides. With gem-disubstituted cyclopropenes, a novel cycloisomerization based on ring-opening nucleophilic attack and rearrangement is observed. Alternatively, some gem-disubstituted cyclopropenes give dimerizations of the intermediate carbene.
烯基环丙烯与Cp*RuCl(cod)反应生成烯基双环[3.1.0]己烷、双环[4.1.0]庚烷和双环[5.1.0]辛烷。该反应在环丙烯开环时的区域选择性与氯化金的反应相反。对于偕二取代的环丙烯，观察到一种基于开环亲核进攻和重排的新型环异构化反应。另外，一些偕二取代的环丙烯会使中间体卡宾发生二聚反应。
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